DE2247331A1 - Neuer carbaminsaeureester sowie seine herstellung und verwendung als insektenbekaempfungsmittel - Google Patents
Neuer carbaminsaeureester sowie seine herstellung und verwendung als insektenbekaempfungsmittelInfo
- Publication number
- DE2247331A1 DE2247331A1 DE19722247331 DE2247331A DE2247331A1 DE 2247331 A1 DE2247331 A1 DE 2247331A1 DE 19722247331 DE19722247331 DE 19722247331 DE 2247331 A DE2247331 A DE 2247331A DE 2247331 A1 DE2247331 A1 DE 2247331A1
- Authority
- DE
- Germany
- Prior art keywords
- tert
- manufacturing
- acid ester
- carbamic acid
- insect repellent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 title 1
- 239000000077 insect repellent Substances 0.000 title 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 title 1
- 239000002917 insecticide Substances 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- JFGVTUJBHHZRAB-UHFFFAOYSA-N 2,6-Di-tert-butyl-1,4-benzenediol Chemical compound CC(C)(C)C1=CC(O)=CC(C(C)(C)C)=C1O JFGVTUJBHHZRAB-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 238000011161 development Methods 0.000 claims description 2
- MCNIWXBRJAKNJH-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl) N-methylcarbamate Chemical compound CNC(OC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C)=O MCNIWXBRJAKNJH-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 241000238631 Hexapoda Species 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000012360 testing method Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 2
- 241001674044 Blattodea Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 2
- LLAPDTLOSXJGRH-UHFFFAOYSA-N 2,3-ditert-butylcyclohexa-2,5-diene-1,4-dione Chemical compound CC(C)(C)C1=C(C(C)(C)C)C(=O)C=CC1=O LLAPDTLOSXJGRH-UHFFFAOYSA-N 0.000 description 1
- -1 4-hydroxyphenyl ester Chemical class 0.000 description 1
- 241001122767 Theaceae Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- BIWJNBZANLAXMG-YQELWRJZSA-N chloordaan Chemical compound ClC1=C(Cl)[C@@]2(Cl)C3CC(Cl)C(Cl)C3[C@]1(Cl)C2(Cl)Cl BIWJNBZANLAXMG-YQELWRJZSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011158 quantitative evaluation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18728371A | 1971-10-07 | 1971-10-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2247331A1 true DE2247331A1 (de) | 1973-04-19 |
Family
ID=22688345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722247331 Pending DE2247331A1 (de) | 1971-10-07 | 1972-09-27 | Neuer carbaminsaeureester sowie seine herstellung und verwendung als insektenbekaempfungsmittel |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS4844426A (cg-RX-API-DMAC10.html) |
| AR (1) | AR202088A1 (cg-RX-API-DMAC10.html) |
| AU (1) | AU462724B2 (cg-RX-API-DMAC10.html) |
| BR (1) | BR7206871D0 (cg-RX-API-DMAC10.html) |
| CA (1) | CA999597A (cg-RX-API-DMAC10.html) |
| DE (1) | DE2247331A1 (cg-RX-API-DMAC10.html) |
| ES (1) | ES407364A1 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2156058B1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1376489A (cg-RX-API-DMAC10.html) |
| IT (1) | IT966228B (cg-RX-API-DMAC10.html) |
| NL (1) | NL7213585A (cg-RX-API-DMAC10.html) |
| ZA (1) | ZA726579B (cg-RX-API-DMAC10.html) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1375961A (fr) * | 1962-09-17 | 1964-10-23 | Geigy Ag J R | Stabilisation de matières organiques, notamment du polypropylène, au moyen de dérivés d'hydroxyphényl-carbamates |
-
1972
- 1972-09-06 CA CA151,008A patent/CA999597A/en not_active Expired
- 1972-09-26 ZA ZA726579A patent/ZA726579B/xx unknown
- 1972-09-27 DE DE19722247331 patent/DE2247331A1/de active Pending
- 1972-09-27 GB GB4463172A patent/GB1376489A/en not_active Expired
- 1972-09-28 AU AU47191/72A patent/AU462724B2/en not_active Expired
- 1972-10-03 JP JP47098677A patent/JPS4844426A/ja active Pending
- 1972-10-04 BR BR6871/72A patent/BR7206871D0/pt unknown
- 1972-10-05 FR FR7235281A patent/FR2156058B1/fr not_active Expired
- 1972-10-06 IT IT53221/72A patent/IT966228B/it active
- 1972-10-06 NL NL7213585A patent/NL7213585A/xx unknown
- 1972-10-06 AR AR244515A patent/AR202088A1/es active
- 1972-10-06 ES ES407364A patent/ES407364A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4844426A (cg-RX-API-DMAC10.html) | 1973-06-26 |
| AU462724B2 (en) | 1975-07-03 |
| IT966228B (it) | 1974-02-11 |
| NL7213585A (cg-RX-API-DMAC10.html) | 1973-04-10 |
| FR2156058B1 (cg-RX-API-DMAC10.html) | 1976-08-20 |
| CA999597A (en) | 1976-11-09 |
| GB1376489A (en) | 1974-12-04 |
| BR7206871D0 (pt) | 1973-09-18 |
| ES407364A1 (es) | 1976-02-16 |
| FR2156058A1 (cg-RX-API-DMAC10.html) | 1973-05-25 |
| ZA726579B (en) | 1973-06-27 |
| AU4719172A (en) | 1974-04-04 |
| AR202088A1 (es) | 1975-05-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |